Syntheses based on α-azidooximes: II. Preparation of 6,7-dihydrotriazolopyrazinones from aliphatic nitro compounds

Semakin, Artem N.; Sukhorukov, Alexey Yu.; Lesiv, Alexey V.; Khomutova, Yu. A.; Ioffe, Sema L.

doi:10.1134/s1070428007080234

Cited by 6 publications

(2 citation statements)

References 7 publications

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“…Semakin et al 101 reported that α-azidooximes, readily obtained from aliphatic nitro compounds, were cleanly converted into previously unknown pyrazinones 313. Here, oximes 310 reacted with DMAD via [3+2] cycloaddition at room temperature affording triazoles 311.…”

Section: Scheme 85mentioning

confidence: 99%

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Neochoritis

Zarganes‐Tzitzikas

Stephanidou‐Stephanatou

2014

Synthesis

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This review presents the recent progress in the chemistry of dimethyl acetylenedicarboxylate (DMAD). The interest in and applications of this powerful reagent with more than 135 years of history have greatly increased in the last 10 years, further proving its versatility. Undoubtedly, DMAD can be a multi-tool in the quest of molecular complexity and diversity. The extreme structural diversity of the products described in this review illustrates the powerful potential of DMAD as a building block in organic synthesis.

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Section: Scheme 85mentioning

confidence: 99%

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Neochoritis

Zarganes‐Tzitzikas

Stephanidou‐Stephanatou

2014

Synthesis

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“…1b, 23a,25 Note that in these cases the additional functionalities in the starting azide did not tolerate the aqueous reactions due to partial hydrolysis. 26 Apparently, the warnings relating to the possible instability of organophosphorus compounds in water resulted in its limited application in organophosphorus synthesis (the known examples comprise the Wittig, Kabachnik-Fields, aza-Michael reactions and synthesis of functionalized stabilized phosphorus ylides via the three-component reaction of triphenylphosphine, dialkyl acetylenedicarboxylates and various nucleophiles). 27 We have found that cycloaddition of ω-phosphorylalkyl azides 1a,b to DMAD 2a proceeded rapidly in water as a sole solvent without a catalyst to afford 4-phosphorylalkyl-1,2,3-triazoles 3a,b in excellent yields and did not affect the ester groups at the phosphorus atom.…”

Section: Resultsmentioning

confidence: 99%

Water as a promoting media for 1,3-dipolar cycloaddition of phosphorylated azides to internal alkynes

Аrtyushin¹,

Matveeva²,

Бушмаринов³

et al. 2012

Arkivoc

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The 1,3-cycloaddition of ω-phosphoryl azides to activated internal alkynes such as dimethyl acetylenedicarboxylate and tetramethyl acetylenediphosphonate as well sodium azide to tetramethyl acetylenediphosphonate readily proceeds in water without any co-solvent or additive to afford the corresponding phosphorylated 1,2,3-triazoles in excellent yields. The ester group in carbalkoxy function of these compounds can be easily converted to carbamido group via the reaction with amines in MeOH thereby expanding the range of potentially biologically active heterocyclic aminophosphonates of such type.

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